(2R,6S)-2-Allyl-6-phenyl-1,2,3,6-tetrahydropyridine

Base Information

• Chemical Name: (2R,6S)-2-Allyl-6-phenyl-1,2,3,6-tetrahydropyridine
• CAS No.: 175478-20-3
• Molecular Formula: C14H17N
• Molecular Weight: 199.29100
• DSSTox Substance ID: DTXSID90361293
• Nikkaji Number: J708.365C
• Wikidata: Q82143565
• Mol file: 175478-20-3.mol

Synonyms:175478-20-3;(2R,6S)-2-ALLYL-6-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE;(2R,6S)-6-phenyl-2-prop-2-enyl-1,2,3,6-tetrahydropyridine;rac-(2R,6S)-2-allyl-6-phenyl-1,2,3,6-tetrahydropyridine;(2R,6S)-6-Phenyl-2-(prop-2-en-1-yl)-1,2,3,6-tetrahydropyridine;Oprea1_743372;DTXSID90361293;MFCD01240129;AKOS022184990;BS-37441;(2S,6R)-2-allyl-6-phenyl-1,2,3,6-tetrahydropyridine;(2R)-2alpha-Allyl-6beta-phenyl-1,2,3,6-tetrahydropyridine

Chemical Property of (2R,6S)-2-Allyl-6-phenyl-1,2,3,6-tetrahydropyridine

Chemical Property:

• Vapor Pressure: 0.00128mmHg at 25°C
• Boiling Point: 298.3oC at 760 mmHg
• Flash Point: 136.2oC
• PSA: 12.03000
• Density: 0.952g/cm3
• LogP: 3.55070
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 199.136099547
• Heavy Atom Count: 15
• Complexity: 226

Purity/Quality:

97% ^*data from raw suppliers

rac-(2R,6S)-2-allyl-6-phenyl-1,2,3,6-tetrahydropyridine 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCC1CC=CC(N1)C2=CC=CC=C2
• Isomeric SMILES: C=CC[C@@H]1CC=C[C@H](N1)C2=CC=CC=C2

Technology Process of (2R,6S)-2-Allyl-6-phenyl-1,2,3,6-tetrahydropyridine

There total 1 articles about (2R,6S)-2-Allyl-6-phenyl-1,2,3,6-tetrahydropyridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 53.0%

pyridine (110-86-1) + Triallylborane (688-61-9,53588-88-8,90721-85-0,151452-33-4,151452-35-6) + phenyllithium (591-51-5) → 2-phenylpyridine (1008-89-5) + trans-2-allyl-6-phenyl-1,2,3,6-tetrahydropyridine (175478-20-3)

Guidance literature:

pyridine; phenyllithium; In diethyl ether; at 0 ℃; for 1h;

Triallylborane; In diethyl ether; at -30 - 10 ℃; for 0.5h;

With methanol; In diethyl ether; at -30 - 20 ℃;

DOI:10.1007/BF01431124

Reference yield:

trans-2-allyl-6-phenyl-1,2,3,6-tetrahydropyridine (175478-20-3) → (2S,6S)-2-Allyl-6-phenyl-1,2,3,6-tetrahydro-pyridine

Guidance literature:

With Triallylborane; sodium hydroxide; Yield given. Multistep reaction; 1.) 195 deg C, 2 h, 2.) methanol, 0-20 deg C;

DOI:10.1016/S0040-4039(97)00953-2

Reference yield:

trans-2-allyl-6-phenyl-1,2,3,6-tetrahydropyridine (175478-20-3) → trans-2-allyl-6-phenylpiperidine + cis-2-allyl-6-phenylpiperidine

Guidance literature:

With tetrabutylammonium perchlorate; In N,N-dimethyl-formamide; for 2h; Electrolysis; Hg cathode;

DOI:10.1007/BF02496263

upstream raw materials:

pyridine

Triallylborane

phenyllithium

Refernces

• 1、 Bubnov,Klimkina,Dekaprilevich,Struchkov. "Synthesis and molecular structure of trans-2-allyl-6-phenyl-1,2,3,6-tetrahydropyridine hydrochloride". . p. 2595 - 2597. Retrieved 2007/10/03.